Sodium Bicarbonate → tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 2193158Notes

Reaction equation

HRID 2193158 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:14][C:15](=[O:23])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O:25]=[C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]1[CH2:36][CH:37]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:14][C:15](=[O:23])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:8]1[CH2:9][CH2:10][N:11]([CH2:37][CH2:36][N:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:34]=[CH:35][C:26]2=[O:25])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397888(2-oxoquinoxalin-1(2H)-yl)acetaldehydeHCID 59398033HCID 59398033, compound

Product 1

HCID 59398373tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateYield 96.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 3 mL of dichloromethane solution containing 0.18 g of tert-butyl(2-oxo-2-(pyridin-2-ylamino)ethyl)(piperidin-4-yl)carbamate, 0.10 g of (2-oxoquinoxalin-1(2H)-yl)acetaldehyde and 30 μl of acetic acid were added and stirred at room temperature for 2 hours. To the reaction mixture, 0.17 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to give 0.26 g of tert-butyl(2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale yellow foam.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed sequentially with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-fde927945ba2402eab3654e1d44108f3
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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